The St. Valentine's Day Massacre

The most intriguing aspects of the 1929 St. Valentine’s Day Massacre are not its known facts and events—dramatic as they were—but speculation, conjecture and inference about what cannot be known for sure about it.

Anyone with the slightest interest in Al Capone, Prohibition, Chicago crime or just the history of crime in general surely knows the essential facts of the massacre. Just as a reminder:

* Torrio, with Capone, arranged the killing of Dion O’Banion in 1924, Then Capone arranged the killing of O’Banion’s successor, Hymie Weiss (’26). After a police detective then killed Weiss’s successor, Vincent “Schemer” Drucci (’27), leadership of the North Side gang devolved on George “Bugs” Moran. When Moran had the idiot idea of hijacking Capone shipments of top quality booze (Old Log Cabin) from Detroit, Capone set up one of his signature killings.

* Although Moran maintained a business headquarters in the Loop, and his gang generally hung out about two miles north at the Wigwam, a bar in the Marigold Hotel, his booze warehouse remained the focus of gang activity. It occupied a garage (for the gang’s beer trucks) at 2122 North Clark, on the near North Side, the sign outside reading “S.M.C. Cartage.”

* Capone arranged for some never-identified free-lance hijackers to sell Moran at least one load of Old Log Cabin at a good price, with promise of more to come. Then the hijackers offered a really big load at the excellent price of $57 a case, to be delivered to Moran at the Clark Street garage on February 14, 1929—a date that found Capone still vacationing at his Palm Island, Florida, home. Indeed, Capone had been summoned on that St. Valentine’s Day to the office of the Dade County solicitor for a 12:30 meeting with a New York assistant DA investigating the recent murder of Frankie Yale (which Capone had, in fact, orchestrated).

* Lookouts had moved into rooming houses at 2119 and 2135 North Clark, across the street from the garage/warehouse. During the early morning, the watchers saw seven men (and one dog) drift into the place, all there by around 10 am. Probably the last to arrive

was Albert R. Weinshank, who ran a speakeasy and was Moran’s point man for muscling into Chicago’s cleaning and dyeing industry. He bore a considerable resemblance to Moran in his chunky, middle-height build, and that day wore a hat and gray overcoat that matched Moran’s usual winter garb. The watchers could easily mistake him for Moran—who, in fact had not yet arrived.

* About 10:30, a Cadillac that looked exactly like a detective squad car, complete with a siren, running-board gong and gun rack behind the driver’s seat, pulled up, having just endured a slight fender-bender with a delivery truck. Four men got out, leaving the driver at the wheel, and entered the garage. Two of the four wore police uniforms. This may have been seen by Moran, himself, plus two of his henchmen, all three approaching the garage when the Cadillac arrived and the “police” went in. All three naturally skedaddled.

* Inside, the seven were lined up against a wall and blasted with sub-machinegun and shotgun fire. All but one died instantly, the other dying in the hospital early that afternoon, refusing to tell the cops anything. No one hurt the dog; but Highball wasn’t talking either.

* Witnesses saw four men exit the garage, the two in civilian clothes with their hands in the air, covered by the two in uniform. All four drove off in the Cadillac, soon found—partly dismantled and partly burned—in a rented garage about two miles away, next to the Circus Café, headquarters of Claude “Screwy” Maddox, a Capone ally.

* The two sub-machineguns that ballistics identified as the murder weapons were found ten months later in the possession of Fred R. “Killer” Burke, when he senselessly shot a policeman, following a trifling auto accident in Saint Joseph, Michigan. Burke was a flake with no known ties to Capone. He died years later in a Michigan prison, never tried for the St. Valentine’s Day Massacre.

* In fact, no one ever stood trial for it.

Those are the central facts of the Massacre, and the only known material facts. And even they include one that is not truly a fact, but only highly probable speculation and inference: that it was Capone who arranged the set-up with the freelance hijackers, and who therefore was behind the Massacre. No proof that he ordered it ever surfaced.

The trouble is—as one highly knowledgeable Capone buff once put it—“The Saint Valentine’s Day Massacre never really made sense.” Another responded that the Beer Wars were over once Moran lost his main muscle (the Gusenberg brothers) and three of his key operatives ( Heyer, Kachellek and Weinshank; the other two victims, May and Schwimmer were, respectively, a low-level gang member, then functioning as a beer-truck mechanic, and a hapless groupie).

But the Beer Wars would have ended with Moran’s solo death. He was the last possible inheritor of North Side leadership, and a very poor last. Even a flake like Schemer Drucci had taken precedence over him. So why kill so many? Capone had seen what happened when he killed only three at the same time (though, to be sure, one was an assistant state’s attorney, having a night out with his gangster pals): it triggered a crackdown that cost Capone millions. Surely he could anticipate the furor that would follow seven simultaneous deaths.

So was it Capone? Some theorists have speculated that it was the work of real policemen, miffed at missed payoffs, some that it was an intra-gang squabble; one thought that it was an outside group of “hillbilly gangsters.” Legend had Moran saying, “Only Capone’s gang kills like that.” He didn’t (see the Myths page); but if Moran had said it, he would have been referring to the ferocity and number of the killings whereas it was really the cleverness and care of the planning, imaginative set-up and flawless execution of the plan that truly signaled a Capone killing. Only Capone’s gang killed like that.

Then why a massacre that truly did not make sense? That predictably caused all manner of problems for Capone and cost him a fortune? That proved the impetus for his downfall?

We can only speculate. But one theory does make sense and squares with the known facts. Most experts agree that Capone’s two premiere gunmen, John Scalise and Alberto Anselmi, were in on it. They were great at killing but had shown themselves not great at thinking. One of Capone’s smartest men and key lieutenants, Jack McGurn, was almost surely part of the planning, but was too well known and too easily recognizable to be at the scene. Had the killers gone into the garage, picked up a phone and called Capone in Florida or McGurn nearby and reported that they had seven people lined up, one of whom they thought was Moran—now what?—chances are they would have been told to either pretend it was a routine shakedown and get out or, at most,“arrest” the one they thought Moran (and maybe the ferocious Gusenberg brothers), leave and do the killing quietly, body or bodies disposed of both discretely and discreetly to avoid the appearance of massacre.

Anselmi and Scalise

Less than three months later, Capone famously bludgeoned Scalise and Anselmi at a banquet. The obvious reason was because the two had contrived the goofy notion that they could stage a coup, along with the head of the Unione Siciliana, and supplant Capone. Assuming the pair had indeed been the senior gang members in the garage, might Capone’s fury also have been stoked by their part in the un-thinking slaughter that was causing him so much trouble and money and would cost him even more in the months and years to come?

Sheer speculation. But the St. Valentine’s Day Massacre may very well have been a carefully set-up plan that simply got out of hand.

You will find a full discussion of the Massacre, with all the facts—including such minutia as the name of the driver who had that fender-bender with the murder car—in Chapters 19 and 20 of the book, MR. CAPONE. For details, click here: Know More.